Prostitute Stories: My Worst Dates

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Prostitute Stories: My Worst Dates
Most of my stories so far have focused on my best/luckiest run ins with hookers. These are the small percentage of dates that include girls who have fallen for me, girls who were insatiable freaks, insanely beautiful girls, horny 18 year olds, threesomes, girls with giant tits, ex pornstars etc. If you’ve been following me regularly then you know I’ve told stories about all of these things. What’s always bugged me is that when I only tell the stories about these rare amazing dates it gives a false impression of what the hobby is actually like. Some of you have written me inspired by my stories and interested in hitting the streets to try things out for yourself. I always try to manage expectations. It’s highly HIGHLY unlikely you’ll meet some hot 18 year old ex pornstar with bigtits that wants to have a threesome with you for the weekend and falls in love. The truth is 9 times out of 10 you will drive around for a couple of hours until you stumble upon an average to below average looking woman. She will not be interested in sex at all just looking for d**gs, or money, or both. The sex itself is usually rushed and not that great and the girls are almost never truly interested. That is what almost all of my dates are like of course I don’t tell you those stories because, well, they’re boring. After talking to another xham user the thought occurred to me the other extreme might also be interesting. Why don’t I try the opposite and tell some stories of the few times I’ve had truly, truly, god awful dates? The one’s that have gone completely wrong. Let’s start off with my worst date by far.

Popeye Joe

“Look! No, no no! You’re twisting up my words! Obviously he looks like a descent black guy. Like the respectable type. He looks like a good guy it was a compliment! All I’m saying is that there’s blacks and then there’s niggers. You know, and then there’s spics and so on.”
“Stop it Joe! Stop it! You’ve got no class you know that? Why do you have to act like garbage?”
“Don’t get upset with me! Chris Rock said that shit now that’s a fucking smart black guy!
“You know I don’t have a racist bone in my body and if you ask me nigger isn’t even a racist word. I’ve met black niggers, I’ve met white niggers, I’ve met puerto rican niggers. I’m not the racist! You’re the racist for thinking just because I’m talking about niggers I’m talking about black people and that’s fucked up Colleen. You get what I’m sayin right bro?” He pats me on the shoulder.

I don’t say a word just stare in silence. I had been up all night driving around and didn’t find a single girl. I started around midnight and It wasn’t until six in the morning (yea I know I’m a fucking head case) when I turned the street and saw this skinny older brunette with a ponytail sitting on the side of the street. I picked her up and she invited me over to her place. Her place is in the projects. These are actually the same housing projects where Sherry and Kerry live they’re a few buildings over and at this point I had not met them yet. My Junky ex girlfriend is about 2 miles south of here I don’t think I’d met her yet either. My date is staying here with her room mate Joe.
“What’s up they call me Popeye Joe”.
Popeye Joe is about 5’8” probably in his 40’s and built like a fucking tank. He’s all muscle, tatoos, shaved bald, with big ears sticking out the side of his head. He looks like a boxer.
“Yea I been boxing since I was 14 or 15”.
Holy shit he literally is a boxer.

“All these guys in the street think they’re tough. They’re fucking pussies. A real fighter has discipline you practice everyday so that when you need your body to do something it can do it. These fucking slobs out here just sit on the stoop and drink beer and before you know it they’re punching each other in the face. That’s not fighting they’re slobs.
Joe bends over and does a bump of what I’m assuming is coke.
“You should have seen me back in the day man. I was a quick little bastard. It’s like first I square off with a guy and wait for an opening and then Bam it’s lights out.”
He starts shadowboxing and before you know it he’s throwing jabs in front of my face. I feel like I’m trapped in a cage with a lion desperately trying to not make any sudden movements afraid that he’ll actually attack. Yet somehow that doesn’t stop me from checking out his roomate, my date’s, ass in the background.

This muscle bound, racist, trained fighter, high on coke is throwing jabs at my god damn face yet all I can think about is fucking some scrawny whore’s pasty pancake ass. What the hell is wrong with me? I stopped thinking about her long enough to remember that I should pray to god to get me out of this situation alive.

I know you’re wondering why don’t I just leave? Well once I entered the room they expect me to give her money for the date if I tried to leave trust canlı bahis şirketleri me there would be problems and I’m not going to pay without fucking her.
“Get away from him you fucking idiot. Come on lets go to the room.”
I follow my date into the room and he follows us. She stops him at the door and shuts it in his face. He yells through the door.
“I live here too and I can’t even get a look?”
Soon after I can hear the radio blasting outside. Remember it’s like six in the morning.
Colleen is not a pretty girl. She’s got a squat wrinkled face and she’s missing most of her teeth I’ve never cared about that and even if I did she was the only girl out there. This is going to happen no matter what she looked like.
We get undressed and she gets me hard. No teeth may not look pretty but trust me there’s nothing that can compare to the feeling a set of slippery wet gums gliding across your stiff hard rod. I’m hard in no time and I climb on top of her.
The sex is alright but I can tell she’s the type that’s trying to get me to cum as soon as possible. Certain girls will try to lay in certain positions or kegel the hell out of your dick to get you to cum fast. Given the circumstances I don’t really blame her. Things were going ok until the bed started rocking and she started moaning. Once Popeye Joe could hear us fucking it was like a shark catching the scent of blood in the water he starts going crazy. Boom, boom boom! He’s pounding on the door.
“You having fun in there Coleen? You taking all that black meat you fucking slut!?” He goes on and on like this.
“You fucking bitch! You’ll let him screw you but I can’t get any? You won’t even let me watch!? You stupid cunt!”
She tells me they’re just room mates but I’m really good at reading people and I’m getting the sense that this guy might be a little jealous.

“Shut the fuck up Joe! Leave us alone. Don’t listen to him baby just ignore him.”
I’ve got her legs spread missionary I continue to pump her determined to bust my nut so I can get the hell out of there. Colleen lovingly cradles my head and is whispering in my ear.
“Just ignore him. It’s ok he’s not going to do anything he’s all show.”
Then dude starts losing his mind!
“Okay you asked for it bitch!”
Boom! It sounded like he hit the door with a bat or a hammer or something. I jump up rip the condom off and toss it on the floor and start grabbing all my shit.
“Fuck this! I’m out of here. Good luck!”
Thank god we we’re on the first floor I throw on my shirt and jeans and hop out the window. I’m sure I left my underwear or socks or something behind but I didn’t care I ran to my car, and didn’t look back. That’s the last time I ever saw Popeye Joe.

The Hot Redhead

I brought home this cute WSW a redhead in her early 20’s, tall, fair skin, cute freckles on her nose, smoking body and amazing ass. I couldn’t wait to see this girl naked. As soon as she got her clothes off I bent her over to get a look at that perfect bubble she was hiding in her shorts. Before we got started she turned to me and let me know right away.
“I don’t do anal so don’t even think about it.”
. . . Ok I wasn’t thinking about it but now I know where she stands on the issue. Good to know. I get hard strap up and begin to push my head in spreading her lips apart. She’s very tight and dry I’m getting nowhere. She spits in her hand for some natural lubrication and I give it a second try. Jesus this girl is tight but I manage to make it in. I slowly start to pump her and that tight little pink snapper pushes me out. She immediately flinches.
“Not my ass!”
I assure her it’s ok I’m not going anywhere near her ass. She bends over and I enter her once again. She’s loosening up and getting into it. She’s still tight as hell but she’s wet now I have no problem gliding against the grip of her walls until . . . pop she pushes me out again. I grab her by the hips and pull her back towards me. The tip of my penis grazes her lips and she flips out her hand immediately flying back to cover over her asshole.
“Watch it!”
I spent the next 10 minutes attempting to have the worst sex ever. Imagine you’re fucking a girl and every 30 seconds she flinches and you have to hear “Careful my ass! Watch it! Not in my asshole!” Something must have traumatized this poor girl. Eventually I had to just give up which of course sucked. She was cute, young, with a great body and where I was living at the time it was beyond rare to find a streetwalker like that. I decide to drive her back.

On the way she asks if we could stop at the gas station to pick some stuff up. We go in and I go get a soda and head to the front. She’s looking at the sandwiches and at one point asks the cashier lady if the condiments are free. Weird question but I don’t think anything of it. The cashier starts ringing me up and we get to chatting while we wait for my date to canlı kaçak iddaa return. She’s taking forever and eventually I hear the cashier yell out.
“Just what the hell do you think you’re doing!?”
I look behind me and there’s my date with a sub sandwich under her arm and both hands are stuffing ketchup and mustard packets into her pockets and into her shorts. The packets are literally falling out of her shorts. At the same time she’s got open mayonnaise packets on the floor and mayo smeared on her face.
“What the hell are you doing?”
“You said they were free.”
I start apologizing to the cashier who is furious. My date also apologizes and starts taking the condiments out of her shorts and placing them back in the bin.
“Stop that! Just stop it! Nobody’s going to want to eat that shit when it’s been down your pants! What the hell is wrong with you two? Are you on d**gs?”
“No I’m not on d**gs. I didn’t know she was going to . . .”
“Get the hell out of here! I don’t ever want to see either one of you in here again.”

We get back in the car and my date is baffled as to why the cashier was yelling at her.
“I don’t get it she said they were free. You heard her right?”
I dropped the redhead off and never saw her again. . . Ok that’s a lie. I saw her walking the streets the next week and even knowing she was batshit crazy I couldn’t help myself. She was wearing those little shorts again and she just looked so good I thought maybe it would be better the second time around. It wasn’t.

The Crazy Drunk

I’ve fucked my fare share of drunk girls I’ve already shared a few of those stories. When it comes to a girl that’s been drinking my rules are different. You may have noticed in every story where I’ve fucked a drunk girl she is the one who initiates. I’m personally not comfortable doing anything with someone who’s drunk unless they clearly indicate in some way that they want sex. So normally I’ll simply pull up and offer them a ride and see what they say. Sometimes that’s all they want is the ride and I’m perfectly happy to do so not everything has to be about sex at that moment. There are times when offering a woman a ride has blossomed into friendships and yes sex down the line so I’ve learned to just go with the flow and see what happens.

Any way It’s very late past closing time for the bars and I turn the corner onto this street where I see a woman who looks a bit tipsy crossing. Now remember I only respond if she initiates. I pull over preparing to offer her a ride and before I’ve even stopped the car she runs to my passenger side window and starts banging on it. No joke, this is what she was screaming word for word.
“Hey let me in your car so I can suck your dick!”
She starts pulling on the locked door handle I made a decision that I would regret later that night. I unlocked the door and let her in. This crazy, petite, red headed, monster of a woman, swings the door open and falls into the car. She immediately starts climbing all over me and kissing me. The strong smell of liquor is wafting from her mouth into my nostrils. She fumbles around with my belt buckle and when she gets it free, stuffs her hands down my briefs and grabs me by the dick. She’s clumsy, pulling and yanking me hard, dives down and proceeds to give me a messy, sloppy, awful blowjob. Hey who am I to complain it’s still a blowjob. Her head’s bobbing up and down she’s gagging every time it hits her throat. I’m nervous she’s going to puke on my seat so I’m actually trying to stop her from going so deep. She’s laying across the passenger seat across the center console with both legs dangling out the passenger door which is still open. Yes that means the interior lights are still on. I try to get her to close the door but she looks at me like I’m speaking a foreign language. It’s late though,everything’s closed, and no one is on the street so I figure what the hell and lean back and just enjoy the fun. One or two cars passed by but they weren’t paying attention. We were only at it for about 2 minutes or so and when this big semi truck comes roaring down the street and stopped at the light right across from us.

I start to try and cover up I couldn’t reach for the door so I just shut off the cabin lights off. He didn’t even notice us which is a good thing because from his vantage point he should be able to see right into the car. Just as I started to relax again this bitch lifts her head from out of my lap, looks out and yells.
“Hey I want to suck your cock”. She then climbs up sticking her head out of my driver side window, arm reaching out towards the truck.
“Hey you give me your cock! Hey! Hey! Did you hear me? Get over here and give me your cock!”
The dude looks over and see’s me wrestling to pull her back into the car and starts laughing his ass off. He honks his horn and takes off once again leaving us alone on that empty canlı kaçak bahis street. I remember being surprised that the guy didn’t try to stay and watch or even try to get some for himself. To be honest if he would have asked to join us I wouldn’t even mind and she was clearly more than willing to get down on a threeway. I guess that’s the difference between me and normal people because if the roles were reversed there’s no way I would have just taken off. After a few more minutes of the clumsiest blowjob I’ve ever had she was ready to fuck and so was I. She unzipped her pants and started taking them off and I had to convince her to keep them on. My place was a short 10 minute drive away so I sped over there as fast as I could while she continued to fondle me.

Once we got to my apartment I tried to sneak her in quickly and silently before she started yelling out any more expletives about my cock to wake my neighbors up.
Once inside we sloppily groped and kissed each other falling onto my couch. She pulls her shirt off and sticks her tiny little tits in my mouth and I stick my hand down the back of her pants and start playing with her pussy. Everything is going great I can tell just by the way she’s acting the sex is going to be wild as hell. She pushes me off of her and rips her clothes off then jumps on top of me and starts fucking my brains out. She’s got a tight muscular skinny body she’s thrusting her hips and you can see every muscle flex. We were going hard at it for a while before she suddenly just stops.
“Hey dude wait this aint right you didn’t give me any money man.”
“What are you serious?”
“Yea man you’ve got to pay for the pussy man give me some cash”
Up until now given how we met I didn’t think she was a hooker at all. I reach into my pants for my wallet and before I can even pull the money out of the damn thing she starts fucking me again forgetting that she even brought it up. She takes me by the neck, leans back, pulling me on top of her. I fuck her hard and she’s spreading her legs wide apart. She’s moaning and cursing, and cumming, I’m getting really turned on when out of nowhere.
POW! This chick punched me in the fucking face! Well not exactly she actually punched me on the side of my head. This wasn’t playful, it wasn’t rough sex. She swung with her full might trying to strike me. I’m in pure shock and she starts yelling.
“What the fuck do you think you’re doing mother fucker!? I’m fucking gay you asshole! I’m a lesbian!”
“What the hell are you talking about? You’re the one who wanted to fuck me.”
“Dude are you a retard or something? What don’t you get? I like girls! I’m gay! Wait till my girlfriend finds out what you did. She’s going to kick your fucking ass.”

We stand there staring at each other for a bit. I’m dumbfounded not sure what to do.
“Why are you looking at me like that? Come here so I can suck your cock.”
She gets back down on her knees and grabs my dick getting ready to put it in her mouth again. I’m so horny and stupid I’m about to let her do it and then I come to my senses. This chick just clocked me in the head. What if she decides she’s gay again when my dick is in her mouth? Fearful of any damage to my family jewels I quickly tuck away my Dwayne ‘The Rock’ Johnson and inform her that she needs to go.
I help her get dressed, repeatedly fighting off more attempts to suck my dick. She gets annoyed and starts yelling then begins throwing things off my table. I’m certain my neighbors can hear us now. What the fuck was I thinking bringing this crazy drunk into to my home!? All I want to do now is just get her the hell out of my place so the neighbors don’t call the cops. I managed to get us both dressed, shoes are on, we’re ready to go. I turn to open the front door and in that split second that I turned to grab the doorknob and then turned back around to face her she took that opportunity to once again try and punch me. This time aiming for the back of my head.

Her reflexes were very slow. By the time I turned back around, like Neo in the matrix, I could see her punch hurtling towards me in slow motion and I quickly dodged her incoming punch. This caused her to lose her balance and fall. Unfortunately she was near one of my table stands. This particular stand has a swinging glass door and I often forget to close the damn thing. I watch her disappear from my view and hear a loud PLANG! As she fell onto the glass door and onto my floor.
My heart was pounding and I was scared to look down. The worst thoughts were running through my head I’m sure the glass cracked impaling her as she fell down. I gather the courage to look down and luckily she’s fine. The door pulled right out of the socket and the glass panel was in one whole piece. God was looking out for both me and her that day because I’m sure if that socket was stronger the force would have caused that glass to break. I pick her up off the floor, put her in the car and drove off rushing her back to where I found her. This was my own dumb fault I should have never picked her up. I looked at it as a life lesson and vowed to never do something like that again.


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